I have 2 dirt and snow seasons on my modded 300. Here's what I have settled on for a setup. Porting and head cut, 42 thousandths squish, any less and you will need race fuel and lose over rev. Scalavini pipe, it works waaay better than any other pipe, I have tried pretty much every one. Boyseen rad valve and pro series reeds. Modified exhaust manifold, weld up the top outside so you can grind out the inside enough to match ports. 38mm carb, 40mm works but you lose too much bottom IMO, every brand has its quirks... lectron, kehin, smart carb. SX ignition makes a noticeable difference, comes on quicker and revs faster, if it doesn't add hp the seat of the pants feel sure doesnt agree. Red PV spring. This setup has outrun pretty much every 450 I've run it against! As far as the 330 kit vs 300, the 330 pulls noticeably harDer off the bottom and the 300 pulls harder on top. I don't know which is better but I wouldn't go 330 unless I burnt a cylinder, the other downfall of the 330 is it vibrates a lot. After riding a lot of 300s in every configuration possible it's pretty apparent that if you do a few of the mods it doesn't do much. An engine is an air pump with 3 stages, intake, combustion and exhaust, if you don't increase the amount of air in all three places you just aren't going to gain much efficiency. Good luck!
Ooh and one more thing, run an EGT Guage! It will make life a lot easier, I've ran stock carbs with JD reccomendations, lectron and smart carb, none of their reccomended setups were close, some of them were off far enough to burn up a motor in the first full pull. Figure on spending the first few rides getting a baseline setting, carbs take work, especially on a modded bike, every bike and every environment has a different setup.